4-Nitrobenzaldehyde → Diethyl [2-(4-nitrophenyl)ethenyl]phosphonate

HRID 1378966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1378966
CC[O-].[Na+].[N+:5]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)([O-:7])=[O:6].[CH2:16](P(=O)(OCC)OCC)[P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]>CO>[CH2:19]([O:18][P:17]([CH:16]=[CH:12][C:11]1[CH:14]=[CH:15][C:8]([N+:5]([O-:7])=[O:6])=[CH:9][CH:10]=1)(=[O:24])[O:21][CH2:22][CH3:23])[CH3:20]

Komponenten

5

Edukt 3

HCID 5414-NitrobenzaldehydeHCID 15455Tetraethyl methylenediphosphonateHCID 2723922Sodium ethoxide2×

Produkt 1

HCID 53749636Diethyl [2-(4-nitrophenyl)ethenyl]phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodium ethylate (4.95 g, 72.8 mmol) is added to a solution of 4-nitrobenzaldehyde (10 g, 66.2 mmol) in 200 ml of methanol, and tetraethyl methylenediphosphonate (21 g, 72.8 mmol) is then added dropwise. After 2 h of stirring at room temperature, a further 0.43 g of sodium ethylate and 2 g of tetraethyl methylene diphosphonate are added. After 15 min of stirring at room temperature, the ethanol is evaporated off under vacuum and the residue is bipartitioned in a water/ethyl acetate mixture. The organic phase is washed with water, then dried (MgSO4) and evaporated under vacuum to give the expected product.

Aufarbeitung

  1. additionis then added dropwise
  2. stirringAfter 15 min of stirring at room temperature
  3. customthe ethanol is evaporated off under vacuum
  4. washThe organic phase is washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ccec20dabff04adea36862d19b735e8c
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670493

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